厦门大学化学化工学院：《有机化学》课程教学资源（授课教案）第十三章 含氮芳香化合物 Aromatic Nitrogen Compounds

第十三章含氮芳香化合物 Aromatic Nitrogen Compounds

第十三章 含氮芳香化合物 Aromatic Nitrogen Compounds

13.1芳香硝基化合物 Nitroarenes

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 13.1 芳香硝基化合物 Nitroarenes

1311结构( structure) Sp 127 147pm 121 pm

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 13.1.1 结构 (Structure) N O 121 pm 147 pm 127 O sp 2

芳香硝基化合物的共振结构」」 Ar—NO2 O 极限式 离域式 O O 共振式

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 芳香硝基化合物的共振结构 芳香硝基化合物的共振结构 Ar NO 2 N O O N O O N O O N O O 极限式 离域式 共振式

1312制备( Preparation) a We have already seen many examples of a the preparation of aromatic nitro compounds By far the most important route to such compounds is electrophilic aromatic nitration with nitric acid NO CH CH CH CH ①D HNO Ac2O. 20 ⑨D CH CH

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 13.1.2 制 备 (Preparation) „ We have already seen many examples of the preparation of aromatic nitro compounds. By far the most important route to such compounds is electrophilic aromatic nitration with nitric acid. CH 3 CH 3 CH 3 HNO 3 Ac 2O , 20 CH 3 CH 3 CH 3 NO 2

1313硝基化合物的性质 Properties of Nitro Compounds

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 13.1.3 硝基化合物的性质 Properties of Nitro Compounds

131.3硝基化合物的性质 .(Properties of Nitro Compounds) Nitrobenzene and related nitro compounds are generally high boiling liquids. Nitrobenzene have a characteristic odor of 画 almonds. a Nitrobenzene is readily absorbed through the skin and is poisonous ①D NO b.p.210-211℃ ⑨D Pale yellow oil

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 13.1.3 硝基化合物的性质 (Properties of Nitro Compounds) „ Nitrobenzene and related nitro compounds are generally high boiling liquids. „ Nitrobenzene have a characteristic odor of almonds. „ Nitrobenzene is readily absorbed through the skin and is poisonous. NO 2 b.p. 210 –211 Pale yellow oil

CH -NO2 2.4.6-Trinitrotoluene TNT,mp.81℃ a tnt is an important expl losive it is relatively insensitive to shock and is used With a detonator -1, 3, 5-Trinitrobenzene is less sensitive ①D than tnt to shock and has more explosive power, but is more difficult to ⑨D prepare

Organic Chemistry Organic Chemistry Xiamen Xiamen University University NO 2 O 2 N O 2 N CH 3 2,4,6-Trinitrotoluene, TNT, m.p. 81 „ TNT is an important explosive. It is relatively insensitive to shock and is used with a detonator. „ 1,3,5-Trinitrobenzene is less sensitive than TNT to shock and has more explosive power, but is more difficult to prepare

1314芳香硝基化合物的反应 (Reactions of Nitroarenes) nO. 2 硝基上的反应 芳环上的反应

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 13.1.4 芳香硝基化合物的反应 (Reactions of Nitroarenes) NO 2 硝基上的反应 芳环上的反应

Reactivities of Nitro Group The nitro group is relatively stable to many reagents. It is generally inert to acids and most electrophilic reagents It is also stable to most oxidizing agents 9. It reacts with RMgx and strongly basic reagents. The most important reaction of the nitro a group in aromatic compounds is reduction

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Reactivities of Nitro Group „ The nitro group is relatively stable to many reagents. „ It is generally inert to acids and most electrophilic reagents. „ It is also stable to most oxidizing agents. „ It reacts with RMgX and strongly basic reagents. „ The most important reaction of the nitro group in aromatic compounds is reduction